Hydrochloric Acid → (1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

HRID 2395194Notes

Reaction equation

HRID 2395194 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12]([O:14]C(=O)C2C=CC=CC=2)[CH3:13])[CH2:11][O:10]1.C[O-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10709605[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoateHCID 10942334Sodium Methoxide

Product 1

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 800 ml of methanol was dissolved 15.9 g of [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate. To the solution was added 28% methanolic solution (12.9 ml) of sodium methylate with ice cooling and the reaction mixture was stirred at room temperature for 6 hours. To the reaction mixture was added 63.2 ml of 1N aqueous solution of hydrochloric acid and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (gradient eluent; hexane:ethyl acetate=6:1→2:1) to give 9.7 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol as a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by silica gel chromatography (gradient eluent; hexane:ethyl acetate=6:1→2:1)

Sources & evidence

ORD record
ord-8936ecbb8154402d9657a89966333bad
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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